CA2087592C - Ferroelectric liquid crystal compositions containing chiral haloalkoxy tail units - Google Patents

Ferroelectric liquid crystal compositions containing chiral haloalkoxy tail units Download PDF

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Publication number
CA2087592C
CA2087592C CA002087592A CA2087592A CA2087592C CA 2087592 C CA2087592 C CA 2087592C CA 002087592 A CA002087592 A CA 002087592A CA 2087592 A CA2087592 A CA 2087592A CA 2087592 C CA2087592 C CA 2087592C
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CA
Canada
Prior art keywords
phenyl
compound
difluoro
chiral
hexylpyrimidine
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired - Fee Related
Application number
CA002087592A
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English (en)
French (fr)
Other versions
CA2087592A1 (en
Inventor
Michael D. Wand
William N. Thurmes
David N. Walba
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Displaytech Inc
Original Assignee
Displaytech Inc
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Displaytech Inc filed Critical Displaytech Inc
Publication of CA2087592A1 publication Critical patent/CA2087592A1/en
Application granted granted Critical
Publication of CA2087592C publication Critical patent/CA2087592C/en
Anticipated expiration legal-status Critical
Expired - Fee Related legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/26—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/76—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring
    • C07C69/84—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring of monocyclic hydroxy carboxylic acids, the hydroxy groups and the carboxyl groups of which are bound to carbon atoms of a six-membered aromatic ring
    • C07C69/92—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring of monocyclic hydroxy carboxylic acids, the hydroxy groups and the carboxyl groups of which are bound to carbon atoms of a six-membered aromatic ring with etherified hydroxyl groups
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K19/00—Liquid crystal materials
    • C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K19/00—Liquid crystal materials
    • C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
    • C09K19/06—Non-steroidal liquid crystal compounds
    • C09K19/08—Non-steroidal liquid crystal compounds containing at least two non-condensed rings
    • C09K19/10—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings
    • C09K19/12—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings at least two benzene rings directly linked, e.g. biphenyls
    • C09K19/126—Compounds containing at least one asymmetric carbon atom
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K19/00—Liquid crystal materials
    • C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
    • C09K19/06—Non-steroidal liquid crystal compounds
    • C09K19/08—Non-steroidal liquid crystal compounds containing at least two non-condensed rings
    • C09K19/10—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings
    • C09K19/20—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings linked by a chain containing carbon and oxygen atoms as chain links, e.g. esters or ethers
    • C09K19/2007—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings linked by a chain containing carbon and oxygen atoms as chain links, e.g. esters or ethers the chain containing -COO- or -OCO- groups
    • C09K19/2021—Compounds containing at least one asymmetric carbon atom
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K19/00—Liquid crystal materials
    • C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
    • C09K19/06—Non-steroidal liquid crystal compounds
    • C09K19/34—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring
    • C09K19/3441—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having nitrogen as hetero atom
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K19/00—Liquid crystal materials
    • C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
    • C09K19/06—Non-steroidal liquid crystal compounds
    • C09K19/34—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring
    • C09K19/3441—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having nitrogen as hetero atom
    • C09K19/345—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having nitrogen as hetero atom the heterocyclic ring being a six-membered aromatic ring containing two nitrogen atoms
    • C09K19/3458—Uncondensed pyrimidines
    • C09K19/3463—Pyrimidine with a carbon chain containing at least one asymmetric carbon atom, i.e. optically active pyrimidines
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K19/00—Liquid crystal materials
    • C09K19/52—Liquid crystal materials characterised by components which are not liquid crystals, e.g. additives with special physical aspect: solvents, solid particles
    • C09K19/58—Dopants or charge transfer agents
    • C09K19/586—Optically active dopants; chiral dopants
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K19/00—Liquid crystal materials
    • C09K19/52—Liquid crystal materials characterised by components which are not liquid crystals, e.g. additives with special physical aspect: solvents, solid particles
    • C09K19/58—Dopants or charge transfer agents
    • C09K19/586—Optically active dopants; chiral dopants
    • C09K19/588—Heterocyclic compounds

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Crystallography & Structural Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Liquid Crystal Substances (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Liquid Crystal (AREA)
CA002087592A 1990-07-20 1991-07-22 Ferroelectric liquid crystal compositions containing chiral haloalkoxy tail units Expired - Fee Related CA2087592C (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US07/556,656 US5130048A (en) 1988-03-04 1990-07-20 Ferroelectric liquid crystal compositions containing chiral haloalkoxy tails units
US556,656 1990-07-20
PCT/US1991/005134 WO1992001765A1 (en) 1990-07-20 1991-07-22 Ferroelectric liquid crystal compositions containing chiral haloalkoxy tail units

Publications (2)

Publication Number Publication Date
CA2087592A1 CA2087592A1 (en) 1992-01-21
CA2087592C true CA2087592C (en) 2002-04-16

Family

ID=24222278

Family Applications (1)

Application Number Title Priority Date Filing Date
CA002087592A Expired - Fee Related CA2087592C (en) 1990-07-20 1991-07-22 Ferroelectric liquid crystal compositions containing chiral haloalkoxy tail units

Country Status (7)

Country Link
US (1) US5130048A (ja)
EP (1) EP0540648B1 (ja)
JP (1) JP3124772B2 (ja)
KR (1) KR0184242B1 (ja)
CA (1) CA2087592C (ja)
DE (1) DE69109680T2 (ja)
WO (1) WO1992001765A1 (ja)

Families Citing this family (21)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5585036A (en) * 1988-03-04 1996-12-17 Displaytech, Inc. Liquid crystal compounds containing chiral 2-halo-2-methyl ether and ester tails
US5422037A (en) * 1988-03-04 1995-06-06 Displaytech, Inc. Ferroelectric liquid crystal compounds containing halogenated cores and chiral haloalkoxy tail units
JPH02138235A (ja) * 1988-07-20 1990-05-28 Takeda Chem Ind Ltd 光学活性化合物、同中間体、該化合物を含有する液晶組成物及び該液晶組成物を用いた液晶光変調装置
US5269965A (en) * 1988-12-28 1993-12-14 Takeda Chemical Industries Optically active compounds, liquid crystal compositions comprising said compounds and liquid crystal optical modulators using said compositions
DE68925954T2 (de) * 1988-12-28 1996-10-17 Hitachi Ltd Optisch aktive Verbindungen, sie enthaltende flüssigkristalline Zusammensetzungen und optische Modulatoren auf Flüssigkristallbasis unter Verwendung dieser Zusammensetzungen
US5380460A (en) * 1991-09-20 1995-01-10 Displaytech, Inc. Ferroelectric liquid crystal compounds containing chiral haloalkoxy tail units and compositions containing them
JP2627679B2 (ja) * 1990-10-19 1997-07-09 高砂香料工業株式会社 光学活性化合物、それを含む液晶組成物及び液晶電気光学素子
JP3078573B2 (ja) * 1990-11-16 2000-08-21 株式会社半導体エネルギー研究所 液晶電気光学装置
JPH0682743A (ja) * 1992-09-04 1994-03-25 Sony Corp 強誘電性液晶組成物
US5462695A (en) * 1994-06-30 1995-10-31 Industrial Technology Research Institute Chiral liquid crystal materials as dopant for ferroelectric liquid crystal compositions
US6471933B1 (en) 1995-02-21 2002-10-29 Anderson Oliver Dotson Ozone-oxidized carbon black composition with low conductivity and improved color
US6737124B2 (en) 2000-12-15 2004-05-18 Displaytech, Inc. Liquid crystal compounds having a silane tail with a perfluoroalkyl terminal portion
US6783812B2 (en) 2000-12-15 2004-08-31 Displaytech, Inc. Alkyl silane liquid crystal compounds
US7195719B1 (en) 2001-01-03 2007-03-27 Displaytech, Inc. High polarization ferroelectric liquid crystal compositions
US6838128B1 (en) 2002-02-05 2005-01-04 Displaytech, Inc. High polarization dopants for ferroelectric liquid crystal compositions
DE102006037079A1 (de) 2006-08-07 2008-02-14 Evonik Degussa Gmbh Ruß, Verfahren zur Herstellung von Ruß und Vorrichtung zur Durchführung des Verfahrens
DE102007060307A1 (de) 2007-12-12 2009-06-18 Evonik Degussa Gmbh Verfahren zur Nachbehandlung von Ruß
ES2368376T3 (es) 2008-12-12 2011-11-16 Evonik Carbon Black Gmbh Tinta para la impresión por chorros de tinta.
CN102585565B (zh) * 2012-03-19 2014-03-19 苏州宝化炭黑有限公司 一种色素炭黑制造方法及装置
JP2014162752A (ja) * 2013-02-25 2014-09-08 Dic Corp 化合物、液晶組成物、及び表示装置
JP2014162751A (ja) * 2013-02-25 2014-09-08 Dic Corp 化合物、液晶組成物、及び表示装置

Family Cites Families (20)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0191860B1 (en) * 1984-06-07 1990-04-18 Seiko Instruments Inc. Liquid crystal compound
US4556727A (en) * 1984-07-18 1985-12-03 University Patents, Inc. Ferroelectric smectic liquid crystals
DE3683062D1 (de) * 1985-02-08 1992-02-06 Ajinomoto Kk Auf polyphenyl basierende esterverbindungen und sie enthaltende fluessigkristalline zusammensetzungen.
DE3515373A1 (de) * 1985-04-27 1986-11-06 Merck Patent Gmbh, 6100 Darmstadt Stickstoffhaltige heterocyclen
JPS62111939A (ja) * 1985-07-23 1987-05-22 Ajinomoto Co Inc 光学活性β−フルオロヒドリン化合物
US4798680A (en) * 1985-10-18 1989-01-17 Canon Kabushiki Kaisha Optically active compound, process for producing same and liquid crystal composition containing same
FR2589623B1 (fr) * 1985-10-31 1989-12-22 Itt Composants Instr Relais electromagnetique
JPS62106985A (ja) * 1985-11-01 1987-05-18 Chisso Corp 複屈折型表示素子用強誘電性カイラルスメクチツク液晶組成物
JPS62258361A (ja) * 1986-01-17 1987-11-10 Toray Ind Inc 光学活性６−置換−ピリジン−３−カルボン酸エステル化合物および液晶
ATE110368T1 (de) * 1986-02-17 1994-09-15 Merck Patent Gmbh Optisch aktive verbindungen.
JPH0739393B2 (ja) * 1986-03-26 1995-05-01 チッソ株式会社 ２−（４′−アルコキシフエニル）−５−アルキルピリジン
JPS63264573A (ja) * 1986-04-24 1988-11-01 Toray Ind Inc 光学活性６−置換−ピリジン−３−カルボン酸エステル化合物および液晶
US4777280A (en) * 1986-07-01 1988-10-11 University Patents, Inc. Phenylbenzoate 1-cyanoalkoxy compounds
US4695650A (en) * 1986-09-24 1987-09-22 University Of Colorado Foundation Liquid crystal compounds and compositions containing same
DE3633968A1 (de) * 1986-10-06 1988-04-07 Hoechst Ag Chirale aryl-2,3-epoxyalkyl-ether und deren entsprechende thioverbindungen und ihre verwendung als dotierstoff in fluessigkristall-phasen
EP0267585B1 (en) * 1986-11-10 1993-09-15 Canon Kabushiki Kaisha Fluoroalkane derivative, its composition and liquid crystal device using same
JPS63137983A (ja) * 1986-11-28 1988-06-09 Chisso Corp ゲストホスト型表示素子用強誘電性液晶混合物
JP2538578B2 (ja) * 1987-02-02 1996-09-25 チッソ株式会社 ２−置換アルキルエ−テル類および液晶組成物
WO1989002425A1 (en) * 1987-09-09 1989-03-23 MERCK Patent Gesellschaft mit beschränkter Haftung Fluorinated oligophenyls and their use in liquid crystal materials
US5051506A (en) * 1988-03-04 1991-09-24 Displaytech, Inc. Ferroelectric liquid crystal compounds containing chiral haloalkyoxy tail units and compositions containing them

Also Published As

Publication number Publication date
CA2087592A1 (en) 1992-01-21
WO1992001765A1 (en) 1992-02-06
EP0540648B1 (en) 1995-05-10
US5130048A (en) 1992-07-14
DE69109680T2 (de) 1995-10-12
JP3124772B2 (ja) 2001-01-15
DE69109680D1 (de) 1995-06-14
KR0184242B1 (en) 1999-04-01
JPH06501929A (ja) 1994-03-03
EP0540648A1 (en) 1993-05-12
EP0540648A4 (en) 1993-08-04

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